US8932786B2 - Metal azo pigments and pigment preparations produced therefrom - Google Patents

Metal azo pigments and pigment preparations produced therefrom Download PDF

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US8932786B2
US8932786B2 US13/933,412 US201313933412A US8932786B2 US 8932786 B2 US8932786 B2 US 8932786B2 US 201313933412 A US201313933412 A US 201313933412A US 8932786 B2 US8932786 B2 US 8932786B2
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pigment
formula
metal
compound
metal azo
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US20140016072A1 (en
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Hans-Ulrich Borst
Frank Linke
Heinz-Josef FUELLMANN
Stephan Michaelis
Dirk Pfuetzenreuter
Sabine Endert
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Lanxess Deutschland GmbH
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/22—Monoazo compounds containing other metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
    • C09B62/40—Azo dyes
    • C09B62/415—Metal complex azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters

Definitions

  • the invention relates to new metal azo pigments, to methods for producing them, to pigment preparations comprising these metal azo pigments and also to their use, especially for producing colour filters, and also to the colour filters themselves.
  • Colour filters are chiefly employed today in liquid crystal displays and screens, colour resolution instruments, and sensors.
  • One known example are the flatscreens on personal computers.
  • the colours may be applied, for example, by colouring a base layer (e.g.
  • the colour-imparting pigments are present in fine distribution (dispersed) in a UV-curable photoresist.
  • This photoresist, as well as the pigment is generally composed of the following components: binder resin, polymerizable monomer, photoinitiator, and optionally a solvent. Preparation takes place, for example, by first finely dispersing the pigment in the form of a concentrate in a solvent and optionally binder resin, and adjusting the dispersion immediately prior to application together with the monomer and the photoinitiator and also, optionally further components.
  • the pigmented photoresist is applied uniformly to the substrate, glass for example, by means of the method known as “spin coating”, for example, and is subjected to preliminary drying, UV exposed through a photomask, developed, using a generally inorganic-alkaline solution, to give the desired colour element patterns, and the coating is cleaned and optionally aftercured. This operation is repeated for each colour, i.e. generally 3 times for a trichromitism in the colours red, green and blue, for example.
  • EP-A-947563 describes specific azopyrazolones for use in colour filters.
  • Specific pigments employed in colour filters in accordance with the prior art are disclosed for example in JP-A-11-217514 and JP-A-11-209631, and especially the pigment Colour Index Pigment Yellow 150 in JP-A-11-209632. With regard to the requirements described, however, these pigments are still in need of improvement.
  • EP-A-1 146 087 as the yellow component of the green colour, a metal azo pigment is described.
  • the yellow-green colour component is preferably composed of the CI Pigment Green 36 and/or CI Pigment Green 58 and a yellow metal azo pigment.
  • the yellow-green colour component advantageously has very high chromaticity and transparency.
  • the yellow pigment must have maximum chromaticity and transparency.
  • the yellow pigment ought at the same time not itself to be greenish, in order, for example, to allow better blending of Pigment Green 36, which as an individual component is much too green.
  • a small shift in the hue of the yellow pigment in the ‘red’ direction, and/or an increase in the chroma implies a dramatic improvement in this yellow pigment as a shading component for, for example, a Pigment Green 36 or 58.
  • the additive effect of the respective three colour filters ought to result in complete light absorption.
  • EP-A 1 591 489 has already described new pigment preparations with enhanced hue brightness as yellow components.
  • These pigment preparations comprise mixtures of particular metal complexes, preferably 1:1 nickel complex of azobarbituric acid, with small amounts of an iron compound and also at least one further metal compound.
  • New yellow metal azo pigments have been found which are outstandingly suitable for tinting green hues of yellow pigments, for example of CI Pigment Green 36, in pigment preparations in the context of the production of colour filters.
  • the invention therefore relates to metal azo pigments comprising the adduct of
  • metal azo pigments comprising the adduct of
  • metal azo pigments comprising the adduct of
  • the amount of metal ions from the series Zn 2+ and Ni 2+ is 95 to 100 mol % and the amount of metal ions selected from the series Cu 2+ , Al 3+ 2/3 , Fe 2+ , Fe 3+ 2/3 , Co 2+ and Co 3+ 2/3 is 0 to 5 mol %, based in each case on one mole of all of the compounds of the formula (I),
  • metal azo pigments comprising the adduct of
  • metal azo pigments comprising the adduct of
  • the metal azo compounds of the formula (I) that are present in the metal azo pigments of the invention comprise chemical hybrid compounds in which the Ni and Zn atoms, and also, optionally, further metal ions M, are incorporated in a common crystal lattice. This difference can be shown experimentally through the different X-ray diffractograms for the physical mixtures and for the chemical hybrid compounds.
  • the X-ray diffractograms of the chemical hybrid compounds of the metal azo pigments of the invention comprising in each case the adduct of the Ni/Zn azo compound and melamine, according to Examples 3 to 5, differ characteristically from the X-ray diffractograms of the physical mixtures of the individual pigments, as is clear from a comparison of the measurement values in Tables 3 to 5 with the measurement values in Tables 6 to 8.
  • alkyl denote, for example, straight-chain or branched C 1 -C 6 -alkyl, which optionally may be substituted one or more times by identical or different substituents, for example by halogen, such as chlorine, bromine or fluorine; —OH, —CN, —NH 2 or C 1 -C 6 -alkoxy.
  • halogen such as chlorine, bromine or fluorine
  • the metal azo pigments of the invention are adducts of a) metal azo compounds of the formula (I) with b) compounds of the formula (II).
  • Adducts here are generally composite molecules. The bond between the molecules may be made for example by intermolecular interactions or Lewis acid-base interactions or by coordinative bonds.
  • the term “adduct” is therefore intended for the purposes of the present invention to encompass, generally, all kinds of incorporation and addition compounds.
  • incorporation compound or “addition compound” in the sense of the present invention are intended to mean, for example, compounds which are formed on the basis of intermolecular interactions such as Van der Waals interactions or else Lewis acid-base interactions. How the incorporation proceeds is dependent not only on the chemical properties of the component to be incorporated but also on the chemical nature of the host lattice. Such compounds are frequently also referred to as intercalation compounds. Chemically speaking, this refers to the incorporation of molecules, ions (rarely also atoms) into chemical compounds.
  • inclusion compounds known as clathrates. These are two-substance compounds in which a guest molecule is incorporated in a lattice or cage comprising a host molecule.
  • incorporation compound or “addition compound” in the sense of the present invention are also to be understood to refer to mixed incorporation crystals (or interstitial compounds).
  • Such a compound is a chemical, non-stoichiometric, crystalline compound of at least two elements.
  • incorporación compound or “addition compound” are also to be understood in the sense of the present invention to refer to compounds which are formed on the basis of coordinative bonds or complex-type bonds.
  • examples of such compounds include mixed substitution crystal or mixed replacement crystal, in which at least two substances form a joint crystal and in which the atoms of the second component are located at regular lattice positions of the first component.
  • Suitable incorporation/addition compounds are, generally, acyclic and cyclic organic compounds, examples being aliphatic and aromatic hydrocarbons, which may be substituted, for example by OH, COOH, NH 2 , substituted NH 2 , CONH 2 , substituted CONH 2 , SO 2 NH 2 , substituted SO 2 NH 2 , SO 3 H, halogen, NO 2 , CN, —SO 2 -alkyl, —SO 2 -aryl, —O-alkyl, —O-aryl, —O-acyl.
  • Carboxamides and sulphonamides are one preferred group of incorporation/addition compounds, and also suitable in particular are urea and substituted ureas such as phenylurea, dodecylurea and others, and also polycondensates thereof with aldehydes, more particular formaldehyde; heterocycles such as barbituric acid, benzimidazolone, benzimidazolone-5-sulphonic acid, 2,3-dihydroxyquinoxaline, 2,3-dihydroxyquinoxaline-6-sulphonic acid, carbazole, carbazole-3,6-disulphonic acid, 2-hydroxyquinoline, 2,4-dihydroxyquinoline, caprolactam, melamine, 6-phenyl-1,3,5-triazine-2,4-diamine, 6-methyl-1,3,5-triazine-2,4-diamine, cyanuric acid.
  • urea and substituted ureas such as phenylurea, dodecy
  • incorporation/addition compound used in accordance with the invention as incorporation/addition compound are those of the formula (II). Especially preferred in this context is melamine.
  • incorporation/addition compounds are polymers, preferably water-soluble polymers, examples being ethylene-propylene oxide block polymers, preferably having a M n of greater than or equal to 1000, more particularly of 1000 to 10 000 g/mol, polyvinyl alcohol, poly(meth)acrylic acids, modified cellulose, such as carboxymethylcelluloses, hydroxy-ethyl- and -propylcelluloses, methyl- and ethylhydroxyethylcelluloses.
  • polymers preferably water-soluble polymers, examples being ethylene-propylene oxide block polymers, preferably having a M n of greater than or equal to 1000, more particularly of 1000 to 10 000 g/mol, polyvinyl alcohol, poly(meth)acrylic acids, modified cellulose, such as carboxymethylcelluloses, hydroxy-ethyl- and -propylcelluloses, methyl- and ethylhydroxyethylcelluloses.
  • the amount of compound of the formula (II) forming an adduct with the metal azo compounds of the formula (I) is generally 5% to 300 mol %, preferably 10 to 250 mol % and more particularly 100 to 200 mol %, based in each case on one mole of compound of the formula (I).
  • the metal azo pigment of the invention preferably possesses a specific surface area (m 2 /g) of 50 to 200 m 2 /g, more particularly 80 to 160 m 2 /g, very preferably 100 to 150 m 2 /g.
  • the surface area is determined in accordance with DIN 66131: Determination of the specific surface area of solids by gas adsorption by the method of Brunauer, Emmett and Teller (B.E.T.).
  • the metal azo pigment of the invention consists of the adduct of a) at least two metal azo compounds of the formula (I) and b) at least one compound of the formula (II), in each case in their general and preferred definitions
  • the metal azo pigments of the invention are obtainable by reacting compounds of the formula (I) or their tautomeric form of their alkali metal salts, preferably of their sodium or potassium salts, in the presence of at least one compound of the formula (II) with nickel salts and zinc salts and optionally with one or more metal salts from the series of copper, aluminium, iron and cobalt salts.
  • the present invention further provides a method for producing the metal azo pigments of the invention, which is characterized in that a compound of the formula (Id), or tautomers thereof,
  • the method of the invention is carried out using generally, per mole of compound of the formula (Id), 0.05 to 0.9 mol of at least one nickel salt, 0.05 to 0.9 mol of at least one zinc salt and 0.05 to 0 mol of at least one metal salt from the series of copper, aluminium, iron and cobalt salts.
  • the method of the invention is carried out using, per mole of compound of the formula (Id) 0.05 to 4 mol, preferably 0.5 to 2.5 mol and very preferably 1.0 to 2.0 mol of compound of the formula (II).
  • binary zinc/nickel azo barbituric acid-melamine adducts are 0.05-0.95 mol, preferably 0.2-0.8 mol and very preferably 0.4-0.7 mol of at least one nickel salt and 0.05-0.95 mol, preferably 0.15-0.6 mol and very preferably 0.25-0.45 mol of at least one zinc salt and 0.05-4 mol, preferably 0.5-2.5 and more preferably 1-2 mol of at least one compound of the formula (II).
  • the method of the invention is carried out in general at a temperature from 60 to 95° C. in aqueous solution at a pH below 7.
  • the nickel and zinc salts for use in accordance with the invention and the further metal salts for optional use, from the series of copper, aluminium, iron and cobalt salts, may be used individually or as a mixture with one another, preferably in the form of an aqueous solution.
  • the compounds of the formula (II) may likewise be added individually or as a mixture with one another, preferably in the form of solids.
  • the method of the invention is carried out such that the azo compound of the formula (Id), preferably as Na or K salt, is introduced initially, one or more of the compound or compounds of the formula (II) that are to be incorporated or added, preferably melamine, is or are added, and this charge is thereafter reacted with at least one nickel salt and at least one zinc salt and optionally one or more metal salts from the series of copper, aluminium, iron and cobalt salts, preferably in the form of the aqueous solutions of these salts, preferably at pH levels of less than 7.
  • Suitability for the purpose of adjusting the pH is possessed by aqueous sodium hydroxide solution, aqueous potassium hydroxide solution, sodium carbonate, sodium hydrogen carbonate, potassium carbonate and potassium hydrogen carbonate.
  • Suitable nickel salts and zinc salts are preferably their water-soluble salts, more particularly chlorides, bromides, acetates, formates, nitrates, sulphates, etc.
  • Nickel and zinc salts employed with preference possess a water solubility of more than 20 g/l, more particularly more than 50 g/l at 20° C.
  • Suitable further metal salts from the series of copper, aluminium, iron and cobalt salts are preferably their water-soluble salts, more particularly their chlorides, bromides, acetates, nitrates and sulphates, preferably their chlorides.
  • the metal azo pigments of the invention that are obtained in this way can then be isolated in the form of an aqueous suction filtercake by filtration of their aqueous suspension.
  • This filtercake can be dried by customary drying methods after washing with hot water, for example.
  • drying methods include the paddle drying or the spray drying of corresponding aqueous slurries.
  • the pigment may subsequently be ground.
  • metal azo pigments of the invention are too harsh-grained or too hard for dispersing, for the desired application, they may be converted to soft-grain pigments in accordance, for example, with the technique described in DE-A 19 847 586.
  • the present invention additionally provides pigment preparations comprising at least one metal azo pigment of the invention.
  • the pigment preparations of the invention are preferably solid at room temperature. Besides the metal azo pigment of the invention they may comprise further additions.
  • a dispersant for the purposes of this specification is a substance which stabilizes the pigment particles in their fine particulate form in aqueous media.
  • fine particulate is meant preferably a finely divided state of 0.001 to 5 ⁇ m, more particularly of 0.005 to 1 ⁇ m, very preferably of 0.005 to 0.5 ⁇ m.
  • the preparation of the invention is preferably in finely particulate form.
  • Suitable dispersants are, for example, anionic, cationic, amphoteric or nonionic.
  • the dispersant is used preferably in an amount of 0.1 to 100 wt %, more particularly 0.5 to 60 wt %, based on the metal azo pigment of the invention that is used, in the pigment preparation.
  • the preparation of the invention may of course also comprise further additions.
  • the additions which lower the viscosity of an aqueous suspension and raise the solids content such as carboxamides and sulphonamides, may be added in an amount of up to 10 wt %, based on the preparation.
  • pigment preparations of the invention comprising at least one dispersant as well as the metal azo pigment of the invention.
  • the pigment preparations are preferably solid preparations which are present preferably as powders or granules.
  • the metal azo pigments of the invention are notable for particularly good dispersibility and high colour strength. Chroma and transparency are outstandingly adjustable.
  • the pigment preparations of the invention are outstandingly suitable for all pigment utilities.
  • synthetic, semi-synthetic or natural macromolecular substances such as polyvinyl chloride, polystyrene, polyamide, polyethylene or polypropylene, for example.
  • They can also be used for the solution colouring of natural, regenerated or manmade fibres, such as cellulosic, polyester, polycarbonate, polyacrylonitrile or polyamide fibres, for example, and also for the printing of textiles and paper.
  • the pigments are outstandingly suitable for ink jet applications and for colour filters for liquid crystal displays.
  • Particularly preferred pigment preparations of the invention are those comprising
  • an organic compound selected from the group of terpenes, terpenoids, fatty acids, fatty acid esters and homopolymers or copolymers, such as random or block copolymers having a solubility in pH-neutral water at 20° C. of less than 1 g/l, more particularly less than 0.1 g/l.
  • pigment preparations of the invention in solid form, preferably in the form of powder or granules.
  • the organic compound of component (c) is preferably solid or liquid at room temperature (20° C.) in a standard atmosphere, and, if it is liquid, it has a boiling point of preferably >100° C., more particularly >150° C.
  • Preferred polymers possess both a hydrophilic and a hydrophobic, preferably polymeric, moiety to the molecule.
  • examples of such polymers are random copolymers based on fatty acids or long-chain C 12 -C 22 hydrocarbons and polyalkylene glycols, more particularly polyethylene glycol.
  • Preferred compounds from the group of terpenes, terpenoids, fatty acids and fatty acid esters include the following: ocimene, myrcene, geraniol, nerol, linalool, citronellol, geranial, citronellal, neral, limonene, menthol, for example ( ⁇ )-menthol, menthone or bicyclic monoterpenes, saturated and unsaturated fatty acids having 6 to 22 C atoms, such as, for example, oleic acid, linoleic acid and linolenic acid or mixtures thereof.
  • organic compounds of component (c) are those given above as incorporation/addition compounds, provided that they conform to the criteria desired for the compound of component c).
  • pigment preparations comprise:
  • the pigment preparation of the invention optionally further comprises a surface-active agent e).
  • Suitable surface-active agents e) are, for example, anionic, cationic, amphoteric or nonionic in nature.
  • Suitable anionic surface-active agents are, in particular, condensation products of aromatic sulphonic acids with formaldehyde, such as condensation products of formaldehyde and alkylnaphthalenesulphonic acids or of formaldehyde, naphthalenesulphonic acids and/or benzenesulphonic acids, condensation products of optionally substituted phenol with formaldehyde and sodium bisulphite.
  • surface-active agents from the group of sulphosuccinic esters and also alkylbenzenesulphonates.
  • Alkoxylated fatty acid alcohols are more particularly those saturated or unsaturated C 6 -C 22 fatty acid alcohols having 5 to 120, preferably 5 to 60, more particularly having 5 to 30 ethylene oxide.
  • the products in question are preferably products which are partly hydrolysed, oxidized, propoxylated, sulphonated, sulphomethylated or desulphonated and are fractionated according to known processes, as for example according to the molecular weight or according to the degree of sulphonation. Mixtures of sulphide and kraft lignosulphonates are also highly effective.
  • Particularly suitable lignosulphonates are those having an average molecular weight of between 1000 and 100 000 g/mol, an active lignosulphonate content of at least 80 wt % and preferably a low polyvalent cation content.
  • the degree of sulphonation may vary within wide limits.
  • nonionic surface-active agents include the following: reaction products of alkylene oxides with alkylatable compounds, such as, for example, fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, such as styrene-phenol condensates, carboxamides and resin acids.
  • alkylatable compounds such as, for example, fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, such as styrene-phenol condensates, carboxamides and resin acids.
  • alkylatable compounds such as, for example, fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, such as styrene-phenol condensates, carboxamides and resin acids.
  • alkylphenols having 4 to 12 C atoms in the alkyl radical or
  • Suitable ethylene oxide adducts are especially the alkylatable compounds identified under a1) to e1) with 5 to 120, more particularly 5 to 100, more particularly 5 to 60, very preferably 5 to 30 mol of ethylene oxide.
  • esters of the alkoxylation product of the formula (X) that are known from DE-A 19 712 486 or from DE-A 19 535 246 and which correspond to the formula (XI), and also these esters optionally in a mixture with the parent compounds of the formula (X).
  • the alkoxylation product of a styrene-phenol condensate of the formula (X) is defined as below:
  • esters of the alkoxylation products (X) correspond to the formula (XI)
  • a preferred surface-active agent used is the compound of the formula (XI).
  • a preferred compound of the formula (XI) is a compound in which X is a radical of the formula —CO—(R 19 )—COO ⁇ and R 19 possess the above definition.
  • surface-active agent is a compound of the formula (XI) together with a compound of the formula (X).
  • the surface-active agent preferably comprises 5 to 99 wt % of the compound (XI) and 1 to 95 wt % of the compound (X).
  • the surface-active agent of component e) is used preferably in an amount of 0.1 to 100 wt %, more particularly 0.5 to 60 wt %, based on the pigment employed.
  • the pigment preparation of the invention may of course also comprise further additions.
  • viscosity-lowering or solids-enhancing additions may be introduced in the course of the production of aqueous suspensions, in an amount of up to 10 wt %, based on the preparation.
  • Bases include the following: alkali metal hydroxides, such as, for example, NaOH, KOH or organic amines such as alkylamines, more particularly alkanolamines or alkylalkanolamines.
  • Those particularly preferred include methylamine, dimethylamine, trimethylamine, ethanolamine, n-propanolamine, n-butanolamine, diethanolamine, triethanolamine, methylethanolamine or dimethylethanolamine.
  • urea and substituted ureas such as phenylurea, dodecylurea and others; heterocycles such as barbituric acid, benzimidazolone, benzimidazolone-5-sulphonic acid, 2,3-dihydroxyquinoxaline, 2,3-dihydroxyquinoxaline-6-sulphonic acid, carbazole, carbazole-3,6-disulphonic acid, 2-hydroxyquinoline, 2,4-dihydroxy-quinoline, caprolactam, melamine, 6-phenyl-1,3,5-triazine-2,4-diamine, 6-methyl-1,3,5-triazine-2,4-diamine, cyanuric acid.
  • the base is optionally present in an amount of up to 20 wt %, preferably up to 10 wt %, based on the pigment.
  • the pigment preparations of the invention may also comprise organic and/or inorganic salts.
  • the preparations of the invention consist to an extent of more than 90 wt %, preferably more than 95 wt % and more particularly more than 97 wt % of at least one metal azo pigment of the invention, at least one organic compound of component c) and optionally at least one surface-active agent of component e), and optionally at least one base.
  • the present invention additionally provides a method for producing the pigment preparations of the invention that is characterized in that at least one metal azo pigment of the invention, at least one organic compound of component c) and optionally at least one surface-active agent of component e), and optionally at least one base, are mixed with one another.
  • the use of the metal azo pigments of the invention or of the pigment preparations of the invention for producing colour filters for liquid crystal displays This use may be described below, using as an example the pigment dispersion technique according to the photoresist method.
  • the inventive use of the pigment preparations of the invention for producing colour filters is characterized, for example, in that at least one metal azo pigment of the invention or one pigment preparation of the invention, more particularly a solid pigment preparation, is homogenized optionally with a binder resin and an organic solvent, optionally with addition of a dispersant, and is then subjected, continuously or batchwise, to wet comminution to a particle size by number (determined by electron microscopy) of 99.5% ⁇ 1000 nm, preferably 95% ⁇ 500 nm and more particularly 90% ⁇ 200 nm.
  • suitable wet comminution methods include stirrer or dissolver dispersing, grinding by means of stirred ball mills or bead mills, compounders, roll mills, high-pressure homogenization or ultrasound dispersing.
  • a photoresist is a preparation which comprises at least one photocurable monomer and a photoinitiator.
  • the present invention also provides a method for producing colour filters for liquid crystal displays, which is characterized in that at least one metal azo pigment of the invention or a pigment preparation of the invention, optionally with a binder resin and an organic solvent, is homogenized, optionally with addition of a dispersant, and is subsequently subjected, continuously or batchwise, to wet comminution to a particle size by number (determined electron microscopy) at 99.5% ⁇ 1000 nm, and during the dispersing treatment or thereafter at least one photocurable monomer and a photoinitiator are added.
  • dispersants contemplated include, generally, commercial dispersants such as, for example, polymeric, ionic or nonionic dispersants based for example on polycarboxylic acids or polysulphonic acids, and also polyethylene oxide-polypropylene oxide block copolymers. Furthermore, derivatives of organic dyes may also be used as dispersants or co-dispersants.
  • the formulation comprises (figures based on formulation):
  • the coating of the photoresist onto a plate for the purpose of generating the coloured image element patterns may be accomplished by either direct or indirect application.
  • application techniques include the following: roller coating, spin coating, spray coating, dip coating and air knife coating.
  • suitable plates include the following: transparent glasses such as white or blue glass plate, silicate-coated blue glass plate, synthetic-resin plate or synthetic-resin films based for example on polyester resin, polycarbonate resin, acrylic resin or vinyl chloride resin, and also metal plates based on aluminium, copper, nickel or steel, and also ceramic plates or semiconductor plates with applied photoelectric transfer elements.
  • transparent glasses such as white or blue glass plate, silicate-coated blue glass plate, synthetic-resin plate or synthetic-resin films based for example on polyester resin, polycarbonate resin, acrylic resin or vinyl chloride resin, and also metal plates based on aluminium, copper, nickel or steel, and also ceramic plates or semiconductor plates with applied photoelectric transfer elements.
  • the application may be followed by thermal drying of the coat.
  • Exposure is preferably accomplished by exposing the photosensitive coat to an active light beam, preferably in the form of an image pattern, using a photomask. This cures the coat at the locations exposed.
  • suitable light sources include the following: high-pressure and ultra-high-pressure mercury vapour lamp, xenon lamp, metal halide lamp, fluorescent lamp, and also laser beam in the visible range.
  • Typical development techniques include spraying with or immersing in aqueous alkaline developer solution or in an organic solvent that comprises inorganic alkali such as sodium or potassium hydroxide, for example, sodium metasilicate or organic bases such as monoethanolamine, diethanolamine, triethanolamine, triethylamine or salts thereof.
  • metal azo pigments are preferably characterized in that they are employed alone or in mixtures with other pigments, customary for the production of colour filters, in the colour filters or pigment preparations or formulations for colour filters.
  • pigments may be other metal salts of an azo compound of the formula (I), or pigment preparations based thereon, or else other organic or inorganic pigments.
  • Preferred organic pigments are, for example, those of the monoazo, disazo, laked azo, ⁇ -naphthol, Naphtol AS, benzimidazolone, disazocondensation, azo metal complex, isoindoline and isoindolinone series, and also polycyclic pigments such as, for example, from the phthalocyanine, quinacridone, perylene, perinone, thioindigo, anthraquinone, dioxazine, quinophthalone and diketopyrrolopyrrole series. Additionally, laked dyes such as Ca, Mg and Al lakes of dyes containing sulphonic or carboxylic acid groups.
  • the fraction of metal azo pigment of the invention is preferably 1-99 wt %, more particularly 20-80 wt %, based on the total amount of all pigments used.
  • Particularly preferred are the pigment preparations of the invention and also formulations comprising at least one metal azo pigment of the invention and C.I. Pigment Green 36 and/or C.I. Pigment Green 58 in a ratio of 20 to 80 wt % of metal azo pigment to 80 to 20 wt % of C.I. Pigment Green 36 and/or C.I. Pigment Green 58, preferably of 40 to 60 wt % to 60 to 40 wt %.
  • binder resins which can be used together with the “pigment” or pigment preparation based thereon in colour filters and/or in the formulations for producing colour filters, in accordance for example with the pigment dispersion method; more particularly, film-forming resins known per se are suitable for application in colour filters.
  • binder resins examples include those from the group of the cellulose resins such as carboxymethylhydroxyethylcellulose and hydroxyethylcellulose, acrylic resins, alkyd resins, melamine resins, epoxy resins, polyvinyl alcohols, polyvinylpyrrolidones, polyamides, polyamideimines, polyimides, polyimide precursors such as those of the formula (14), disclosed in JP-A 11 217 514 and esterification products thereof.
  • cellulose resins such as carboxymethylhydroxyethylcellulose and hydroxyethylcellulose
  • acrylic resins alkyd resins
  • melamine resins epoxy resins
  • polyvinyl alcohols polyvinylpyrrolidones
  • polyamides polyamideimines
  • polyimides polyimide precursors such as those of the formula (14), disclosed in JP-A 11 217 514 and esterification products thereof.
  • Examples of such include reaction products of tetracarboxylic dianhydride with diamines.
  • binder resins are those which contain photopolymerizable unsaturated bonds.
  • the binder resins may for example be those constructed from the group of the acrylic resins.
  • Particularly noteworthy in this context are monomers and copolymers of polymerizable monomers such as, for example, methyl(meth)acrylate, ethyl(meth)acrylate, propyl(meth)acrylate, butyl(meth)acrylate, styrene and styrene derivatives, and also copolymers between carboxyl-bearing polymerizable monomers such as (meth)acrylic acid, itaconic acid, maleic acid, maleic anhydride, maleic acid monoalkyl esters, especially with alkyl of 1 to 12 C atoms, and polymerizable monomers such as (meth)acrylic acid, styrene and styrene derivatives, such as ⁇ -methylstyrene, m- or p-methoxyst
  • Examples include reaction products of carboxyl-containing polymeric compounds with compounds which contain both an oxirane ring and an ethylenically unsaturated bond such as, for example, glycidyl(meth)acrylate, acryloyl glycidyl ether and itaconic acid monoalkyl glycidyl ether, etc., and also reaction products of carboxyl-containing polymeric compounds with compounds which contain both a hydroxyl group and an ethylenically unsaturated bond (unsaturated alcohols) such as allyl alcohol, 2-buten-4-ol, oleyl alcohol, 2-hydroxyethyl(meth)acrylate, N-methylolacrylamide, etc.;
  • binder resins additionally it is possible as well for such binder resins to contain unsaturated compounds which possess free isocyanate groups.
  • the equivalence of the unsaturation (molar weight of binder resin per unsaturated bond) of the stated binder resins is 200 to 3000, more particularly 230 to 1000, in order to attain both sufficient photopolymerizability and film hardness.
  • the acid value is generally 20 to 300, more particularly 40 to 200, in order to obtain sufficient alkali developability following film exposure.
  • the average molar weight of the binder resins to be used is between 1500 and 200 000, more particularly 10 000 to 50 000 g/mol.
  • the organic solvents used in the case of the inventive use for the pigment preparations for colour fillers are, for example, ketones, alkylene glycol ethers, alcohols and aromatic compounds.
  • ketones group are as follows: acetone, methyl ethyl ketone, cyclohexanone, etc.; from the group of the alkylene glycol ethers: methyl Cellosolve (ethylene glycol monomethyl ester), butyl Cellosolve (ethylene glycol monobutyl ether), methyl Cellosolve acetate, ethyl Cellosolve acetate, butyl Cellosolve acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glyco
  • solvents are 1,2-propanediol diacetate, 3-methyl-3-methoxybutyl acetate, ethyl acetate, N-hydroxymethyl-2-acetic acid ethyl ester, tetrahydrofuran, etc.
  • the solvents can be used individually or in mixtures with one another.
  • the invention further relates to a photoresist comprising at least one metal azo pigment of the invention or at least one pigment preparation of the invention and at least one photocurable monomer and also at least one photoinitiator.
  • the photocurable monomers contain in the molecule at least one reactive double bond and optionally other reactive groups.
  • Photocurable monomers are understood in this context in particular to be reactive solvents or what are called reactive diluents, from the group, for example, of mono-, di-, tri- and multi-functional acrylates and methacrylates, vinyl ethers, and also glycidyl ethers.
  • Suitable reactive groups additionally present include allyl, hydroxyl, phosphate, urethane, secondary amine and N-alkoxy-methyl groups.
  • the selection of the monomers is guided in particular by the nature and intensity of the type of exposure radiation used, the desired reaction with the photoinitiator, and the film properties. Combinations of monomers can also be used.
  • Photoreaction initiators or photoinitiators are compounds which by virtue of the absorption of visible or ultraviolet radiation form reactive intermediates which are able to set off a polymerization reaction of, for example, the above mentioned monomers and/or binder resins. Photoreaction initiators are likewise common knowledge and may likewise be found in Römpp Lexikon, Lacke und Druckmaschine , Dr. Ulrich Zorll, Thieme Verlag Stuttgart-New York, 1998, pp. 445/446.
  • the invention relates preferably to photoresists comprising
  • An azobarbituric acid (0.3 mol) prepared according to instruction 1 was admixed at 82° C. with 1500 g of distilled water. Thereafter 75.7 g of melamine (0.6 mol) were introduced. Then 0.3 mol of an approximately 30% strength zinc chloride solution was added dropwise. After 3 hours at 82° C., the pH was adjusted to about 5.5 using KOH. This was followed by dilution at 90° C. with about 300 g of distilled water. Then 34 g of 30% strength hydrochloric acid were added dropwise and a temperature of 90° C. was established for 12 hours. Thereafter the pH was adjusted to about 5 using aqueous potassium hydroxide solution.
  • the pigment was subsequently isolated on a suction filter, washed, dried in a vacuum drying cabinet at 80° C., and ground for about 2 minutes in a standard laboratory mill.
  • Porture A adduct of zinc azobarbituric acid and melamine.
  • An azobarbituric acid (0.3 mol) prepared according to instruction 1 was admixed at 82° C. with 1500 g of distilled water. Then 10 g of 30% strength hydrochloric acid were added dropwise, to adjust the pH to 2-2.5. Thereafter 79.4 g of melamine (0.63 mol) were introduced. Then 0.3 mol of an approximately 25% strength nickel chloride solution was added dropwise. After 3 hours at 82° C., the pH was adjusted to about 5.5 using KOH. This was followed by dilution at 90° C. with about 100 g of distilled water. Then 21 g of 30% strength hydrochloric acid were added dropwise and a temperature of 90° C. was established for 12 hours.
  • Example 2 the procedure of Example 2 was repeated, but the nickel chloride solution was replaced by a mixed solution of nickel chloride and zinc chloride.
  • pigment C melamine adduct of zinc/nickel azobarbituric acid, hybrid compound with 25 mol % Zn and 75 mol % nickel
  • pigment D melamine adduct of zinc/nickel azobarbituric acid, hybrid compound with 50 mol % Zn and 50 mol % nickel)
  • pigment E melamine adduct of zinc/nickel azobarbituric acid, hybrid compound with 75 mol % Zn and 25 mol % nickel)
  • the X-ray diffractometry measurements were carried out in a PANalytical EMPYREAN theta/theta reflection diffractometer with PIXcel counter, suitable for the identification of crystalline phases.
  • Sample 7 5.0 g pigment A and 5.0 g pigment B (physical mixture 50 mol % zinc and 50 mol % nickel) not inventive
  • Sample 8 7.5 g pigment A and 2.5 g pigment B (physical mixture 75 mol % zinc and 25 mol % nickel) not inventive
  • the sample holder was then introduced into the sample changer of the diffractometer, and the measurement was performed.
  • the theta values for the samples measured were determined in accordance with the method described above. Measurements on samples 1 to 8 were undertaken in this way. The reflection values determined in these measurements, following background correction, have been reproduced in Tables 1 to 8.
  • the reflections measured have been numbered in the first column.
  • the position of the measured reflections has been reported in the form of 2theta values; in column 3, the 2theta values ascertained have been converted, using the Bragg equation, into d values for the lattice constants.
  • the fourth and fifth columns contain the values for the measured intensities (peak height of the reflections above the background), on the one hand as absolute values in the unit “counts” [cts], and also in their relative intensity, in percent.
  • the intensity values reported in Tables 1 to 8 are background-corrected. This means that the value for the background (of 4100 counts in the case of the instrument used here) was subtracted arithmetically in each case from all of the intensity values measured.
  • the samples 1 to 8 were assembled as indicated above from the pigments prepared according to synthesis Examples 1 to 5. The samples were subsequently converted according to instruction 2 to give the corresponding dispersions. The dispersions 1 to 8 were converted in accordance with instruction 3 and subjected to performance testing. The results in the form of the Y values are set out in Table 10.
  • Test plaques with a layer thickness gradation of 1 mm, 2 mm and 3 mm were produced from the dry pellets on an injection moulding machine with a melt temperature of 240° C., a back pressure of 10 bar and a mould temperature of 60° C.
  • the transmission of 1 mm, 2 mm and 3 mm stages was measured using a spectrophotometer.
  • the spectrophotometer was calibrated by means of the colourless test plaques at 1 mm, 2 mm and 3 mm in each case.
  • the inventive samples 3-5 exhibit increased Y values (for constant x value) in comparison to the non-inventive samples, and are therefore notable for an increased brightness.

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EP2682435B1 (de) 2018-02-28
CN103525120B (zh) 2017-08-29
EP2682434A1 (de) 2014-01-08
TW201420688A (zh) 2014-06-01
EP2682435A1 (de) 2014-01-08
KR102123698B1 (ko) 2020-06-16
JP6141704B2 (ja) 2017-06-07
KR20140005104A (ko) 2014-01-14
ES2663971T3 (es) 2018-04-17

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